Construction of the tetracyclic ring system of diterpene alkaloids cationic [5 + 2] cycloaddition

The ABCD ring system of C 18 /C 19 diterpene alkaloids was constructed via cationic [5 + 2] cycloaddition to forge a bicyclo[3.2.1]octane, an intramolecular aldol reaction to form a seven-membered ring, oxidation of a phenol at the para -position, and introduction of a one-carbon unit via Stille cou...

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Published in:Organic & biomolecular chemistry 2023-06, Vol.21 (22), p.4587-459
Main Authors: Mizuno, Kosuke, Nishiyama, Yoshitake, Yokoshima, Satoshi
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Summary:The ABCD ring system of C 18 /C 19 diterpene alkaloids was constructed via cationic [5 + 2] cycloaddition to forge a bicyclo[3.2.1]octane, an intramolecular aldol reaction to form a seven-membered ring, oxidation of a phenol at the para -position, and introduction of a one-carbon unit via Stille coupling followed by oxidative cleavage of a furan ring. The ABCD ring system of C 18 /C 19 diterpene alkaloids was constructed via cationic [5 + 2] cycloaddition and an intramolecular aldol reaction.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00647f